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Trifluoroacetic acid → 3-(3-Benzenesulfonyl-1H-indol-6-yl)-N-hydroxy-acrylamide

HRID 84198
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 84198
[NH2:1][O:2]C1CCCCO1.[C:9]1([S:15]([C:18]2[C:26]3[C:21](=[CH:22][C:23]([CH:27]=[CH:28][C:29]([OH:31])=O)=[CH:24][CH:25]=3)[NH:20][CH:19]=2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.C(O)(C(F)(F)F)=O>CN(C=O)C.CO>[C:9]1([S:15]([C:18]2[C:26]3[C:21](=[CH:22][C:23]([CH:27]=[CH:28][C:29]([NH:1][OH:2])=[O:31])=[CH:24][CH:25]=3)[NH:20][CH:19]=2)(=[O:16])=[O:17])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 2724699PyBOPHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 674346353-(3-Benzenesulfonyl-1H-indol-6-yl)-acrylic acid

Produkt 1

HCID 760350453-(3-Benzenesulfonyl-1H-indol-6-yl)-N-hydroxy-acrylamide
Ausbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

NH2OTHP (0.04 g, 0.37 mmol) was added to a solution of 24 (0.10 g, 0.31 mmol), PyBOP (0.17 g, 0.33 mmol), triethylamine (0.1 ml, 0.74 mmol) in DMF (1 mL). The reaction mixture was stirred at room temperature for 1 h before it was quenched with water, followed by extraction with EtOAc (15 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (CH2Cl2:CH3OH=30:1:1% NH3(aq)) to give a white solid, which was treated with TFA (0.70 ml, 9.44 mmol) in the presence of CH3OH (15 mL) and stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure to give a white residue, which was recrystallized by CH3OH to afford Compound 24 (0.08 g). 1H NMR (500 MHz, CD3OD): δ 6.45 (d, J=15.8 Hz, 1H), 7.45 (d, J=8.4 Hz, 1H), 7.50-7.65 (m, 5H), 7.81 (d, J=8.4 Hz, 1H), 7.98-8.00 (m, 2H), 8.04 (s, 1H). MS (EI) m/z: 342. HRMS (EI) for C17H14N2O4S (M+): calcd, 342.0674. found, 342.0674.

Aufarbeitung

  1. customwas quenched with water
  2. extractionfollowed by extraction with EtOAc (15 mL×3)
  3. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (CH2Cl2:CH3OH=30:1:1% NH3(aq))
  6. customto give a white solid, which
  7. stirringstirred overnight at room temperature
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. customto give a white residue, which
  10. customwas recrystallized by CH3OH

Quellen und Nachweise

ORD-Eintrag
ord-b2fa865d7e3140c59ece3e036695f756
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846748B2

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